Hydrazine → 4-Bromo-6-hydrazino-isoquinolin-1-ylamine

HRID 2244070Notes

Reaction equation

HRID 2244070 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](F)=[CH:9][CH:10]=2)[C:5]([Br:13])=[CH:4][N:3]=1.[NH2:14][NH2:15].C([O-])(O)=O.[Na+]>C1COCC1>[Br:13][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([NH:14][NH2:15])[CH:7]=2)[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 516892Sodium BicarbonateHCID 250594381-Amino-4-bromo-6-fluoro-isoquinoline

Product 1

HCID 250596924-Bromo-6-hydrazino-isoquinolin-1-ylamineYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1-amino-4-bromo-6-fluoro-isoquinoline (0.1179 g, 0.49 mmol), and hydrazine (0.5 mL) in THF (5 mL) is microwaved at 100° C. for 40 min. Then it is placed in an oil bath and is stirred at 100° C. for 16 h. The reaction mixture is cooled to RT. It is treated with NaHCO3 (satd. aq, 10 mL). The aqueous phase is extracted with EtOAc (2×). The combined organic layers are washed with brine, and dried over MgSO4. The solvent is evaporated and the residue is dried under vacuum to afford 0.079 g (64%) of 4-Bromo-6-hydrazino-isoquinolin-1-ylamine. LC/MS m/z=254 [M+H]+.

Workup

  1. customThen it is placed in an oil bath
  2. temperatureThe reaction mixture is cooled to RT
  3. extractionThe aqueous phase is extracted with EtOAc (2×)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over MgSO4
  6. customThe solvent is evaporated
  7. customthe residue is dried under vacuum

Sources & evidence

ORD record
ord-a1c3fd4690034534a94a4d996ebc6b68
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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